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When I was two years old, my parents took me on a road trip from southern Missouri to California and back, which looks like about 3,300 miles. That appears to be my record in a car, though I don't remember it at all.
Next month we'll do a 2,300 mile road trip through South Dakota, Montana, and Wyoming, which will be a new adult record for me.
I have a vague memory of doing a family trip from Austin to northern Kentucky on a family trip once, which is 1,900 miles. That was pretty much a drive more than a road trip, though. Going to visit some family members for Christmas, so we just had to get there.
As an adult, I think my biggest pleasure trip has been a trip from Denver to the Grand Canyon, passing through Utah on the way out and New Mexico on the way back. That's about 1,500 miles, and we made lots of fun stops, so it counts as a true road trip.
We also drove from Austin to Albuquerque a couple of times for family visits, which is a round trip of 1,400 miles. Those were more drives than road trips, but it was pretty cool to drive through west Texas, so they were fun.
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